John P. Calamia, President

Our Mission

Our mission is to recruit great sales leaders and build great SaaS GTM teams who will take your business to the next level.

Our Firm

We recruit for all GTM functions including enterprise sales, corporate sales, sales enablement, revenue operations, and channels/alliances. Our firm focuses primarily on venture or private equity backed firms with revenues of up to $400M in ARR.

Our Differentiation

Experience is irreplaceable when it comes to making critical talent assessment decisions. We’ve been on both sides of the table—first as a sales leader in fast-growing, highly successful companies, and now as specialists in talent search.

About John P. Calamia, Founder and President – Career Milestones

• 1990-1998 Sales leadership at Sybase. IPO in 1992. Helped grow revenues from $24M to $1B. Established market dominance in the financial services sector. 

• 1997 – First sales leader at Vignette – IPO in 1998

• 2000 – First ever VP of Sales at Riversoft – IPO in 2000. Helped to take the company public in one year. 

• 2001 Founded Calamia and Associates – Launched a boutique search firm in the post dot.com era

• 2006 Partner, Leadership Group Executive Search – Joined an established team of industry leaders from Spencer Stuart, Korn Ferry and Stanton Chase

• 2008 Founded Oak Point Consulting – Launched a 2nd boutique firm focused on technology sales and sales leadership recruiting. 

• 2024 Founded Pioneers and Legends – Created and launched a successful technology networking community of over 300 CXOs, Investors, and Board Advisors in technology.

John has strong relationships with a large network of investors, venture capital firms, and senior executives from some of the world’s most successful technology companies.